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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:47 UTC
Update Date2023-02-21 17:22:29 UTC
HMDB IDHMDB0032613
Secondary Accession Numbers
  • HMDB32613
Metabolite Identification
Common Name3,4-Methylenedioxybenzoic acid
Description3,4-Methylenedioxybenzoic acid, also known as piperonylic acid or 1,3-benzodioxole-5-carboxylic acid, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Based on a literature review very few articles have been published on 3,4-Methylenedioxybenzoic acid.
Structure
Data?1677000149
Synonyms
ValueSource
3,4-MethylenedioxybenzoateGenerator
1,3-Benzodioxole-5-carboxylic acidHMDB
1,3-Benzodioxole-5-carboxylic acid, 9ciHMDB
3, 4-(Methylenedioxy)benzoic acidHMDB
3,4-(Methylenedioxy)-benzoic acidHMDB
3,4-(Methylenedioxy)benzoic acidHMDB
3,4-Dioxymethylenebenzoic acidHMDB
3,4-Methylene dioxybenzoic acidHMDB
5-Benzodioxolecarboxylic acidHMDB
Heliotropic acidHMDB
Piperonylic acidHMDB
Protocatechuic acid methylene etherHMDB
2H-1,3-Benzodioxole-5-carboxylateHMDB
Piperonylic acid, sodium saltHMDB
Chemical FormulaC8H6O4
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
IUPAC Name2H-1,3-benzodioxole-5-carboxylic acid
Traditional Name2H-1,3-benzodioxole-5-carboxylic acid
CAS Registry Number94-53-1
SMILES
OC(=O)C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)
InChI KeyVDVJGIYXDVPQLP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Benzenoid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point229 °CNot Available
Boiling Point324.59 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1424 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.810 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available124.452http://allccs.zhulab.cn/database/detail?ID=AllCCS00001125
Predicted Molecular Properties
PropertyValueSource
Water Solubility13.2 g/LALOGPS
logP1.26ALOGPS
logP1.25ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.08 m³·mol⁻¹ChemAxon
Polarizability15.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.14231661259
DarkChem[M-H]-131.07231661259
DeepCCS[M+H]+132.51930932474
DeepCCS[M-H]-129.80730932474
DeepCCS[M-2H]-165.90130932474
DeepCCS[M+Na]+140.92130932474
AllCCS[M+H]+134.132859911
AllCCS[M+H-H2O]+129.632859911
AllCCS[M+NH4]+138.432859911
AllCCS[M+Na]+139.632859911
AllCCS[M-H]-130.932859911
AllCCS[M+Na-2H]-131.432859911
AllCCS[M+HCOO]-132.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Methylenedioxybenzoic acidOC(=O)C1=CC2=C(OCO2)C=C12561.8Standard polar33892256
3,4-Methylenedioxybenzoic acidOC(=O)C1=CC2=C(OCO2)C=C11425.3Standard non polar33892256
3,4-Methylenedioxybenzoic acidOC(=O)C1=CC2=C(OCO2)C=C11557.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Methylenedioxybenzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C2OCOC2=C11588.0Semi standard non polar33892256
3,4-Methylenedioxybenzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C2OCOC2=C11847.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)splash10-014i-4900000000-70cd469c29d2482d95f02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)splash10-014i-2900000000-4390b1bdc5917c5f26fc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)splash10-014i-0900000000-7a656232e76ad9e209c72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)splash10-014i-4900000000-cef5628d095e3f32ecfd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)splash10-014i-4900000000-70cd469c29d2482d95f02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)splash10-014i-2900000000-4390b1bdc5917c5f26fc2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)splash10-014i-0900000000-7a656232e76ad9e209c72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)splash10-014i-4900000000-cef5628d095e3f32ecfd2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-5900000000-5c0de1857ad6317b0e432017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9830000000-33cb18ddb487b6122ed32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid Linear Ion Trap , negative-QTOFsplash10-00di-0900000000-6fae03ddbf68a91dbc9a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 10V, Positive-QTOFsplash10-014i-0900000000-fdf0ce1dbf59e03574202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 20V, Positive-QTOFsplash10-014i-0900000000-11f8683efcfb6c5396202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 40V, Positive-QTOFsplash10-00di-5900000000-a19edf4a7090e8d4839d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 10V, Negative-QTOFsplash10-014i-0900000000-4d8e4f3c34640b43c05b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 20V, Negative-QTOFsplash10-00xr-0900000000-10b8d66e451092b3d8eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 40V, Negative-QTOFsplash10-006t-9700000000-e2645b4317d232203b0b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 10V, Negative-QTOFsplash10-014i-0900000000-81c3cd21eb6448e5cdfb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 20V, Negative-QTOFsplash10-00di-1900000000-266fcca288a86551c6bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 40V, Negative-QTOFsplash10-014l-8900000000-a37f990c1ac7d5aff64a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 10V, Positive-QTOFsplash10-01ba-0900000000-bfc9a42adac7578d66452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 20V, Positive-QTOFsplash10-01b9-0900000000-6d30ef91858166da41092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 40V, Positive-QTOFsplash10-05fs-4900000000-aa22ba71b3141948e23f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010554
KNApSAcK IDC00031034
Chemspider ID6928
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7196
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1275031
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3,4-Methylenedioxybenzoic acid → 6-(2H-1,3-benzodioxole-5-carbonyloxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
3,4-Methylenedioxybenzoic acid → 2-{[(2H-1,3-benzodioxol-5-yl)(hydroxy)methylidene]amino}acetic aciddetails